5alpha-epoxyalantolactone (CHEBI:65856)

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CHEBI:65856 - 5α-epoxyalantolactone

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ChEBI ID	CHEBI:65856
ChEBI Name	5α-epoxyalantolactone
Stars
ASCII Name	5alpha-epoxyalantolactone
Definition	A sesquiterpene lactone that is the 5α-epoxy derivative of alantolactone. Isolated from the root extracts of Inula helenium, it exhibits antimycobacterial activity.
Last Modified	21 January 2013
Downloads	Molfile

Formula	C15H20O3
Net Charge	0
Average Mass	248.322
Monoisotopic Mass	248.14124
SMILES	[H][C@@]12C[C@@]3(C)CCC[C@H](C)[C@@]34O[C@H]4[C@]1([H])C(=C)C(=O)O2
InChI	InChI=1S/C15H20O3/c1-8-5-4-6-14(3)7-10-11(9(2)13(16)17-10)12-15(8,14)18-12/h8,10-12H,2,4-7H2,1,3H3/t8-,10+,11+,12-,14+,15-/m0/s1
InChIKey	YIQKVCDNUFDAHB-HKKVUVRFSA-N

Species of Metabolite	Component	Source	Comments
Inula helenium (ncbitaxon:55635)	root (BTO:0001188)	PubMed (10364842)

Roles Classification

Biological Roles:	antimycobacterial drug A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:	antimycobacterial drug A drug used to treat or prevent infections caused by Mycobacteria, a genus of actinobacteria. Aerobic and nonmotile, members of the genus include the pathogens responsible for causing tuberculosis and leprosy.

ChEBI Ontology

Outgoing Relation(s)
	5α-epoxyalantolactone (CHEBI:65856) has functional parent alantolactone (CHEBI:2540)
	5α-epoxyalantolactone (CHEBI:65856) has role antimycobacterial drug (CHEBI:64912)
	5α-epoxyalantolactone (CHEBI:65856) has role metabolite (CHEBI:25212)
	5α-epoxyalantolactone (CHEBI:65856) is a epoxide (CHEBI:32955)
	5α-epoxyalantolactone (CHEBI:65856) is a naphthofuran (CHEBI:39270)
	5α-epoxyalantolactone (CHEBI:65856) is a sesquiterpene lactone (CHEBI:37667)

IUPAC Name
(1aR,2S,5aR,6aR,9aR,9bS)-2,5a-dimethyl-9-methylideneoctahydro-2H-oxireno[4,4a]naphtho[2,3-b]furan-8(9H)-one

Registry Numbers	Sources
Reaxys:5031399	Reaxys

Citations